Polymer and organic light-emitting device comprising the same

ABSTRACT

A polymer and an organic light-emitting device including the polymer.

CROSS-REFERENCE TO RELATED APPLICATIONS

This application claims priority to Korean Patent Application No.10-2011-0004532, filed on Jan. 17, 2011, and all the benefits accruingtherefrom under 35 U.S.C. §119, the content of which in its entirety isherein incorporated by reference.

BACKGROUND

1. Field

This disclosure relates to polymers and organic light-emitting devicesincluding the polymers.

2. Description of the Related Art

Organic light-emitting devices are active emission-type devices, and arelightweight, require a small number of components, have a simplemanufacturing process, a high image quality, and a wide viewing angle,perfectly embody high color purity and moving pictures, and operate withlow power consumption at low voltage. Due to such characteristics, theyhave electric characteristics suitable for various electronicapplications

For example, the organic light-emitting device includes an anodedisposed on a substrate, an organic layer including a hole transportlayer, an emitting layer, an electron transport layer, and additionaloptional layers disposed on the anode, and a cathode disposed on theorganic layer.

If a current is applied to the anode and the cathode, holes injectedfrom the anode move to the emitting layer through the hole transportlayer and electrons injected from the cathode move to the emitting layerthrough the electron transport layer. The holes and electrons arerecombined with each other in the emitting layer to generate excitons.Then, the excitons decay radiatively, thereby emitting light having awavelength corresponding to a band gap of a corresponding material.

Materials for use in the organic layer may be classified as suitable forvacuum deposition or suitable for solution coating, according to amethod of forming the organic layer. The material suitable for solutioncoating may be mixed with a solvent to provide a composition suitablefor coating on a substrate, and the composition may be disposed onto asubstrate using a known solution-coating method, such as inkjetprinting, screen printing, or spin coating.

SUMMARY

Provided are polymers having a novel structure.

Also provided are organic light-emitting devices including the polymers.

Additional aspects will be set forth in part in the description whichfollows and, in part, will be apparent from the description, or may belearned by practice of the presented embodiments.

According to an embodiment, a polymer has a repeating unit representedby

Formula 1 below:

wherein, in Formula 1,

in at least one pair of two R groups selected from a pair R₁ and R₂, apair R₃ and R₄, a pair R₅ and R₆, and a pair R₇ and R₈, an atom in eachR group thereof is connected to each other to form a single bond orconnected to each other via a linking group represented by—[C(Q₆)(Q₇)]_(p)—, or R₁ to R₈ are each independently hydrogen,deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitrogroup, a carboxyl group, a substituted or unsubstituted C₁-C₆₀ alkylgroup, a substituted or unsubstituted C₂-C₆₀ alkenyl group, asubstituted or unsubstituted C₂-C₆₀ alkynyl group, a substituted orunsubstituted C₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₆₀cycloalkyl group, a substituted or unsubstituted C₃-C₆₀ cycloalkenylgroup, a substituted or unsubstituted C₆-C₆₀ aryl group, a substitutedor unsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstitutedC₆-C₆₀ arylthio group, a substituted or unsubstituted C₁-C₆₀ heteroarylgroup, —N(Q₁)(Q₂) or —Si(Q₃)(Q₄)(Q₅);

p is an integer of 1 or 2;

Ar₁ to Ar₃ are each independently a substituted or unsubstituted C₆-C₃₀arylene group, or a substituted or unsubstituted C₁-C₃₀ heteroarylenegroup;

a, b, and c are each independently an integer of 1 to 10;

R₁₁ to R₃₉ are each independently hydrogen, deuterium, a halogen atom, ahydroxyl group, a cyano group, a nitro group, a carboxyl group, asubstituted or unsubstituted C₁-C₆₀ alkyl group, a substituted orunsubstituted C₂-C₆₀ alkenyl group, a substituted or unsubstitutedC₂-C₆₀ alkynyl group, a substituted or unsubstituted C₁-C₆₀ alkoxygroup, a substituted or unsubstituted C₃-C₆₀ cycloalkyl group, asubstituted or unsubstituted C₃-C₆₀ cycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₁-C₆₀ heteroaryl group, —N(Q₈)(Q₉), or—Si(Q₁₀)(Q₁₁)(Q₁₂);

Q₁ to Q₁₂ are each independently hydrogen, deuterium, a halogen, ahydroxyl group, a cyano group, a nitro group, a carboxyl group, asubstituted or unsubstituted C_(r) C₆₀ alkyl group, a substituted orunsubstituted C₂-C₆₀ alkenyl group, a substituted or unsubstitutedC₂-C₆₀ alkynyl group, a substituted or unsubstituted C₁-C₆₀ alkoxygroup, a substituted or unsubstituted C₃-C₆₀ cycloalkyl group, asubstituted or unsubstituted C₃-C₆₀ cycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, ora substituted or unsubstituted C₁-C₆₀ heteroaryl group; and

m is an integer of 0 to 5.

The polymer may be used as a phosphorescent host in an emitting layer ofan organic light-emitting device.

According to another embodiment, an organic light-emitting device mayinclude a substrate; a first electrode; a second electrode; and a firstlayer that is disposed between the first electrode and the secondelectrode and includes the polymer as described above.

BRIEF DESCRIPTION OF THE DRAWINGS

The above and other aspects, advantages and features of this disclosurewill become more apparent by describing in further detail embodimentsthereof with reference to the accompanying drawings, in which:

FIG. 1 is a schematic sectional view of an organic light-emitting deviceaccording to an embodiment;

FIG. 2 shows ultraviolet (UV) spectra of polymers 2 and 3 in a solution;

FIG. 3 shows photoluminescence (PL) spectra of polymers 2 and 3 in asolution;

FIG. 4 is a voltage-current density graph of organic light-emittingdevices manufactured according to Examples 2 and 3 and ComparativeExample 1;

FIG. 5 is a voltage-brightness graph of organic light-emitting devicesmanufactured according to Examples 2 and 3 and Comparative Example 1;and

FIG. 6 shows Formula 1-2.

DETAILED DESCRIPTION

The invention now will be described more fully hereinafter withreference to the accompanying drawings, in which various embodiments areshown. This invention may, however, be embodied in many different formsand should not be construed as limited to the embodiments set forthherein. Rather, these embodiments are provided so that this disclosurewill be thorough and complete, and will fully convey the scope of theinvention to those skilled in the art. Like reference numerals refer tolike elements throughout.

The terminology used herein is for the purpose of describing particularembodiments only and is not intended to be limiting. As used herein, thesingular forms “a,” “an” and “the” are intended to include the pluralforms as well, unless the context clearly indicates otherwise. It willbe further understood that the terms “comprises” and/or “comprising,” or“includes” and/or “including” when used in this specification, specifythe presence of stated features, regions, integers, steps, operations,elements, and/or components, but do not preclude the presence oraddition of one or more other features, regions, integers, steps,operations, elements, components, and/or groups thereof. It will befurther understood that the terms “first” and “second” are used todifferentiate one element from another element; they are not intended tospecify any numerical order.

Unless otherwise defined, all terms (including technical and scientificterms) used herein have the same meaning as commonly understood by oneof ordinary skill in the art to which this invention belongs. It will befurther understood that terms, such as those defined in commonly useddictionaries, should be interpreted as having a meaning that isconsistent with their meaning in the context of the relevant art and thepresent disclosure, and will not be interpreted in an idealized oroverly formal sense unless expressly so defined herein.

According to an embodiment, provided is a polymer having a repeatingunit represented by Formula 1 below:

wherein, in Formula 1, in at least one pair of two R groups selectedfrom a pair R₁ and R₂, a pair R₃ and R₄, a pair R₅ and R₆, and a pair R₇and R₈, an atom in each R group thereof may be connected to each otherto form a single bond or connected to each other via a linking grouprepresented by —[C(Q₆)(Q₇)]_(p)—. In Formula 1, p may be 1 or 2.

In an embodiment, in at least one pair selected from a pair R₁ and R₂, apair R₃ and R₄, a pair R₅ and R₆, and a pair R₇ and R₈, an atom of eachR group thereof is connected to each other. Alternatively, each pairselected from a pair R₁ and R₂, a pair R₃ and R₄, a pair R₅ and R₆, anda pair R₇ and R₈, an atom of each R group thereof is connected to eachother. For example, n an embodiment, R₁ and R₂ are connected to eachother to form a single bond, (forming, a carbazole ring for example), adouble bond, or a triple bond, R₃ and R₄ are connected to each other toform a single bond (forming a carbazole ring for example), a doublebond, or a triple bond, R₅ and R₆ are connected to each other to form asingle bond (forming a carbazole ring for example), a double bond, or atriple bond, and R₇ and R₈ are not connected to each other. In anotherembodiment, in each of the pairs R₁ and R₂, R₃ and R₄, R₅ and R₆, and R₇and R₈, an atom of each R group thereof are connected to each other.

In addition, in at least one pair selected from a pair R₁ and R₂, a pairR₃ and R₄, a pair R₅ and R₆, and a pair R₇ and R₈, an atom of each Rgroup thereof is connected to each other, and the resultant structuresmay be the same or different from each other. For example, in each of apair R₁ and R₂, a pair R₃ and R₄, and a pair R₅ and R₆, an atom of eachR group thereof is are connected to each other to form a single bond(forming a carbazole ring for example), and the R groups of a pair R₇and R₈ are connected to each other to form a —CH₂— linking group(forming an acridine ring, for example).

Q₆ and Q₇ in Formula 1 may each be independently hydrogen, deuterium, ahalogen atom, a hydroxyl group, a cyano group, a nitro group, a carboxylgroup, a substituted or unsubstituted C₁-C₁₀ alkyl group, a substitutedor unsubstituted C₂-C₁₀ alkenyl group, a substituted or unsubstitutedC₁-C₁₀ alkoxy group, a substituted or unsubstituted C₆-C₁₄ aryl group,or a substituted or unsubstituted C₁-C₁₄ heteroaryl group.

For example, Q₆ and Q₇ may each be independently hydrogen, deuterium, ahalogen atom, a hydroxyl group, a cyano group, a nitro group, a carboxylgroup, a C₁-C₁₀ alkyl group, or a C₁-C₁₀ alkoxy group, but are notlimited thereto.

Alternatively, in Formula 1, R₁ to R₈ may each be independentlyhydrogen, deuterium, a halogen atom, a hydroxyl group, a cyano group, anitro group, a carboxyl group, a substituted or unsubstituted C₁-C₆₀alkyl group, a substituted or unsubstituted C₂-C₆₀ alkenyl group, asubstituted or unsubstituted C₂-C₆₀ alkynyl group, a substituted orunsubstituted C₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₆₀cycloalkyl group, a substituted or unsubstituted C₃-C₆₀ cycloalkenylgroup, a substituted or unsubstituted C₆-C₆₀ aryl group, a substitutedor unsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstitutedC₆-C₆₀ arylthio group, a substituted or unsubstituted C₁-C₆₀ heteroarylgroup, —N(Q₁)(Q₂), or —Si(Q₃)(Q₄)(Q₅). That is, in this embodiment, noneof a pair R₁ and R₂, a pair R₃ and R₄, a pair R₅ and R₆, and a pair R₇and R₈ are connected to each other.

In a specific embodiment, R₁ to R₈ may each be independently hydrogen,deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitrogroup, a carboxyl group, a substituted or unsubstituted C₁-C₁₀ alkylgroup, a substituted or unsubstituted C₂-C₁₀ alkenyl group, asubstituted or unsubstituted C₁-C₁₀ alkoxy group, a substituted orunsubstituted C₆-C₁₄ aryl group, or a substituted or unsubstitutedC₁-C₁₄ heteroaryl group.

For example, R₁ to R₈ may each be independently hydrogen, deuterium, ahalogen atom, a hydroxyl group, a cyano group, a nitro group, a carboxylgroup, a C₁-C₁₀ alkyl group, or a C₁-C₁₀ alkoxy group, but are notlimited thereto.

In Formula 1, Ar₁ to Ar₃ may each be independently a substituted orunsubstituted C₆-C₃₀ arylene group, a substituted or unsubstitutedC₁-C₃₀ heteroarylene group, a substituted or unsubstituted (C₁-C₁₀alkyl)C₆-C₃₀ arylene group, a substituted or unsubstituted di(C₁-C₁₀alkyl)C₆-C₃₀ arylene group, a substituted or unsubstituted (C₆-C₁₄aryl)C₆-C₃₀ arylene group, a substituted or unsubstituted di(C₆-C₁₄aryl)C₆-C₃₀ arylene group, a substituted or unsubstituted (C₁-C₁₀alkyl)C₁-C₃₀ heteroarylene group, a substituted or unsubstituteddi(C₁-C₁₀ alkyl)C₁-C₃₀ heteroarylene group, a substituted orunsubstituted (C₆-C₁₄ aryl)C₁-C₃₀ heteroarylene group, or a substitutedor unsubstituted di(C₆-C₁₄ aryl)C₁-C₃₀ heteroarylene group.

For example, Ar₁ to Ar₃ may each be independently a substituted orunsubstituted phenylene group, a substituted or unsubstitutedpentalenylene group, a substituted or unsubstituted indenylene group, asubstituted or unsubstituted naphthylene group, a substituted orunsubstituted azulenylene group, a substituted or unsubstitutedheptalenylene group, a substituted or unsubstituted indacenylene group,a substituted or unsubstituted acenaphthylene group, a substituted orunsubstituted fluorenylene group, a substituted or unsubstitutedphenanthrylene group, a substituted or unsubstituted anthrylene group, asubstituted or unsubstituted fluoranthenylene group, a substituted orunsubstituted triphenylenylene group, a substituted or unsubstitutedpyrenylene group, a substituted or unsubstituted chrysenylene group, asubstituted or unsubstituted naphthacenylene group, a substituted orunsubstituted picenylene group, a substituted or unsubstitutedperylenylene group, a substituted or unsubstituted pentaphenylene group,a substituted or unsubstituted hexacenylene group, a substituted orunsubstituted pyrrolylene group, a substituted or unsubstitutedpyrazolylene group, a substituted or unsubstituted imidazolylene group,a substituted or unsubstituted imidazolinylene group, a substituted orunsubstituted imidazopyridinylene group, a substituted or unsubstitutedimidazopyrimidinylene group, a substituted or unsubstituted pyridinylenegroup, a substituted or unsubstituted pyrazinylene group, a substitutedor unsubstituted pyrimidinylene group, a substituted or unsubstitutedindolylene group, a substituted or unsubstituted purinylene group, asubstituted or unsubstituted quinolinylene group, a substituted orunsubstituted phthalazinylene group, a substituted or unsubstitutedindolizinylene group, a substituted or unsubstituted naphthyridinylenegroup, a substituted or unsubstituted quinazolinylene group, asubstituted or unsubstituted cinnolinylene group, a substituted orunsubstituted indazolylene group, a substituted or unsubstitutedcarbazolylene group, a substituted or unsubstituted phenazinylene group,a substituted or unsubstituted phenanthridinylene group, a substitutedor unsubstituted pyranylene group, a substituted or unsubstitutedchromenylene group, a substituted or unsubstituted benzofuranylenegroup, a substituted or unsubstituted thiophenylene group, a substitutedor unsubstituted benzothiophenylene group, a substituted orunsubstituted isothiazolylene group, a substituted or unsubstitutedbenzoimidazolylene group, or a substituted or unsubstitutedisoxazolylene group.

For example, Ar₁ to Ar₃ may each be independently a phenylene group, a(C₁-C₁₀ alkyl)phenylene group, a di(C₁-C₁₀ alkyl)phenylene group, a(C₆-C₁₄ aryl)phenylene group, a di(C₆-C₁₄ aryl)phenylene group, afluorenylene group, a (C₁-C₁₀ alkyl)fluorenylene group, a di(C₁-C₁₀alkyl)fluorenylene group, a (C₆-C₁₄ aryl)fluorenylene group, a di(C₆-C₁₄aryl)fluorenylene group, a phenanthrylene group, a (C₁-C₁₀alkyl)phenanthrylene group, a di(C₁-C₁₀ alkyl)phenanthrylene group, a(C₆-C₁₄ aryl)phenanthrylene group, a di(C₆-C₁₄ aryl)phenanthrylenegroup, a pyridinylene group, a (C₁-C₁₀ alkyl)pyridinylene group, adi(C₁-C₁₀ alkyl)pyridinylene group, a (C₆-C₁₄ arylene)pyridinylenegroup, or a di(C₆-C₁₄ aryl)pyridinylene group, but are not limitedthereto. Nonlimiting examples of the C₆-C₁₄ aryl include phenyl,naphthyl, anthryl, and the like.

According to an embodiment, in Formula 1, Ar₁ to Ar₃ may each beindependently a substituted or unsubstituted phenylene group, asubstituted or unsubstituted fluorenylene group, a substituted orunsubstituted phenanthrylene group, a substituted or unsubstitutedpyridinylene group, or a substituted or unsubstituted phenylpyridinylenegroup, but are not limited thereto.

For example, Ar₁ to Ar₃ may all be the same.

In Formula 1, a, b, and c may each be independently an integer of 1 to10. If a is 2 or more, two or more Ar₁ may be identical to or differentfrom each other, if b is 2 or more, two or more Ar₂ may be identical toor different from each other, and if c is 2 or more, two or more Ar₃ maybe identical to or different from each other.

For example, a, b, and c may each be independently 1, 2, 3, or 4, butare not limited thereto.

In Formula 1, —(Ar₁)_(a)—, —(Ar₂)_(b)—, and —(Ar₃)_(c)— may be identicalto each other. For example, in Formula 1, —(Ar₁)_(a)—, —(Ar₂)_(b)—, and—(Ar₃)_(b)— may all be a phenylene group (Ar₁═Ar₂═Ar₃=phenylene group,a=b=c=1), a biphenylene group (Ar₁═Ar₂═Ar₃=phenylene group, a=b=c=2), atriphenylene group (Ar₁═Ar₂═Ar₃=phenylene group, a=b=c=3), atetraphenylene group (Ar₁═Ar₂═Ar₃=phenylene group, a=b=c=4), afluorenylene group (Ar₁═Ar₂═Ar₃=fluorenylene group, a=b=c=1), aphenanthrylene group (Ar₁═Ar₂═Ar₃=phenanthrylene group, a=b=c=1), apyridinylene group (Ar₁═Ar₂═Ar₃=pyridinylene group, a=b=c=1), or aphenylpyridinylene group (Ar₁═Ar₂═Ar₃=phenylpyridinylene group,a=b=c=1), but are not limited thereto.

In Formula 1, R₁₁ to R₃₉ may each be independently hydrogen, deuterium,a halogen atom, a hydroxyl group, a cyano group, a nitro group, acarboxyl group, a substituted or unsubstituted C₁-C₆₀ alkyl group, asubstituted or unsubstituted C₂-C₆₀ alkenyl group, a substituted orunsubstituted C₂-C₆₀ alkynyl group, a substituted or unsubstitutedC₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₆₀ cycloalkylgroup, a substituted or unsubstituted C₃-C₆₀ cycloalkenyl group, asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstitutedC₆-C₆₀ arylthio group, a substituted or unsubstituted C₁-C₆₀ heteroarylgroup, —N(Q₈)(Q₉), or —Si(Q₁₀)(Q₁₁)(Q₁₂).

For example, R₁₁ to R₃₉ may each be independently hydrogen, deuterium, ahalogen atom, a hydroxyl group, a cyano group, a nitro group, a carboxylgroup, a substituted or unsubstituted C₁-C₁₀ alkyl group, a substitutedor unsubstituted C₂-C₁₀ alkenyl group, a substituted or unsubstitutedC₁-C₁₀ alkoxy group, a substituted or unsubstituted C₆-C₁₄ aryl group,or a substituted or unsubstituted C₁-C₁₄ heteroaryl group.

According to an embodiment, in Formula 1, R₁₁ to R₃₉ may each beindependently hydrogen, deuterium, a halogen atom, a hydroxyl group, acyano group, a nitro group, a carboxyl group, a C₁-C₁₀ alkyl group, or aC₁-C₁₀ alkoxy group, but are not limited thereto.

In Formula 1, R₁₁ to R₁₉, R₂₁ to R₂₃ and R₂₅ to R₃₈ may all be hydrogen,and R₂₀, R₂₄ and R₃₉ may each be independently hydrogen, deuterium, ahalogen, a hydroxyl group, a cyano group, a nitro group, a carboxylgroup, a substituted or unsubstituted C₁-C₁₀ alkyl group, a substitutedor unsubstituted C₂-C₁₀ alkenyl group, a substituted or unsubstitutedC₁-C₁₀ alkoxy group, a substituted or unsubstituted C₆-C₁₄ aryl group,or a substituted or unsubstituted C₁-C₁₄ heteroaryl group. For example,R₂₀, R₂₄, and R₃₉ may each be independently hydrogen, deuterium, ahalogen atom, a hydroxyl group, a cyano group, a nitro group, a carboxylgroup, a C₁-C₁₀ alkyl group, or a C₁-C₁₀ alkoxy group, but are notlimited thereto.

In Formula 1, m may be an integer of 0 to 5. For example, m may be 0, 1,or 2, but is not limited thereto.

In Formula 1 (see Formula 1-1 below), moiety A, moiety C, and moiety Dmay be identical to each other. For example, in Formula 1, moieties A toD, as shown in Formula 1-1 below may all be identical to each other. Bybeing so, hole mobility in a hole transporting part of the polymerincluding the repeating unit represented by Formula 1 may be improved(the hole transporting part of the polymer will be described in detaillater where Formula 1-2 is described).

In an embodiment, the polymer repeating unit represented by Formula 1,may be, for example, represented by Formula 1A below, wherein, inFormula 1, the pair R₁ and R₂ are connected to each other to form asingle bond, the pair R₃ and R₄ are connected to each other to form asingle bond, the pair R₅ and R₆ are connected to each other to form asingle bond, and the pair R₇ and R₈ are connected to each other to forma single bond. In an alternative embodiment, the polymer repeat unitrepresented by Formula 1 may be represented by Formula 1B below,wherein, in Formula 1, the pair R₁ and R₂ are connected to each other toform a —[C(Q₆)(Q₇)]- linking group, the pair R₃ and R₄ are connected toeach other to form a —[C(Q₆)(Q₇)]- linking group, the pair R₅ and R₆ areconnected to each other to form a —[C(Q₆)(Q₇)]- linking group, and thepair R₇ and R₈ are connected to each other to form a —[C(Q₆)(Q₇)]-linking group. In yet another embodiment, the polymer repeat unitrepresented by Formula 1, may be represented by Formula 10 below,wherein, in Formula 1, the pair R₁ and R₂ are connected to each other toform a —[C(Q₆)(Q₇)]₂— linking group, the pair R₃ and R₄ are connected toeach other to form a —[C(Q₆)(Q₇)]₂— linking group, the pair R₅ and R₆are connected to each other to form a —[C(Q₆)(Q₇)]₂— linking group, andthe pair R₇ and R₈ are connected to each other to form a —[C(Q₆)(Q₇)]₂—linking group.

In Formulae 1A, 1B, and 1C, R₁₁ to R₃₉, Q₆, Q₇, Ar₁ to Ar₃, a, b, c, andm are the same as described above with reference to Formula 1.

In an embodiment, in Formulae 1A, 1B, and 1C, R₁₁ to R₃₉ and Q₆ and Q₇may each be independently hydrogen, deuterium, a halogen atom, ahydroxyl group, a cyano group, a nitro group, a carboxyl group, asubstituted or unsubstituted C₁-C₁₀ alkyl group, a substituted orunsubstituted C₂-C₁₀ alkenyl group, a substituted or unsubstitutedC₁-C₁₀ alkoxy group, a substituted or unsubstituted C₆-C₁₄ aryl group,or a substituted or unsubstituted C₁-C₁₄ heteroaryl group; Ar₁ to Ar₃may each be independently a substituted or unsubstituted phenylenegroup, a substituted or unsubstituted fluorenylene group, a substitutedor unsubstituted phenanthrylene group, a substituted or unsubstitutedpyridinylene group, or a substituted or unsubstituted phenylpyridinylenegroup; a, b, and c may each be independently an integer of 1 to 10; andm may be 0, 1, or 2.

In another embodiment, in Formulae 1A, 1B, and 1C, R₁₁ to R₁₉, R₂₁ toR₂₃, and R₂₅ to R₃₈ are all hydrogen, and R₂₀, R₂₄ and R₃₉ are eachindependently hydrogen, deuterium, a halogen atom, a hydroxyl group, acyano group, a nitro group, a carboxyl group, a substituted orunsubstituted C₁-C₁₀ alkyl group, a substituted or unsubstituted C₂-C₁₀alkenyl group, a substituted or unsubstituted C₁-C₁₀ alkoxy group, asubstituted or unsubstituted C₆-C₁₄ aryl group, or a substituted orunsubstituted C₁-C₁₄ hetero aryl group.

In still another embodiment, in Formulae 1A, 1B and 10, Ar₁ to Ar₃ mayeach be independently a phenylene group, a fluorenylene group, aphenanthrylene group, a pyridinylene group, or a phenylpyridinylenegroup, but are not limited thereto; and a, b, and c may each beindependently 1, 2, 3, or 4, but are not limited thereto.

According to an embodiment, the polymer repeating unit represented byFormula 1 may be represented by Formula 1A-1 below, but is not limitedthereto:

wherein, in Formula 1A-1, R₂₀, R₂₄, R₃₉, Ar₁ to Ar₃, a, b, c, and m arethe same as described above with reference to Formula 1.

For example, in Formula 1A-1, R₂₀, R₂₄ and R₃₉ may each be independentlyhydrogen, deuterium, a halogen atom, a hydroxyl group, a cyano group, anitro group, a carboxyl group, a C₁-C₁₀ alkyl group, or a C₁-C₁₀ alkoxygroup, but are not limited thereto; Ar₁ to Ar₃ may each be independentlya substituted or unsubstituted phenylene group, a substituted orunsubstituted fluorenylene group, a substituted or unsubstitutedphenanthrylene group, a substituted or unsubstituted pyridinylene group,or a substituted or unsubstituted phenylpyridinylene group, but are notlimited thereto; a, b, and c may each be independently 1, 2, 3, or 4,but are not limited thereto; and m may be 0, 1 or 2, but is not limitedthereto.

According to an embodiment, in Formula 1A-1, R₂₀ and R₂₄ may each beindependently a C₁-C₁₀ alkyl group, but is not limited thereto; R₃₉ maybe a C₁-C₁₀ alkoxy group, but is not limited thereto; Ar₁ to Ar₃ mayeach be independently a phenylene group, a fluorenylene group, aphenanthrylene group, a pyridinylene group, or a phenylpyridinylenegroup, but are not limited thereto; a, b, and c may each beindependently 1, 2, 3, or 4, but are not limited thereto; and m may be0, 1, or 2, but is not limited thereto.

In an embodiment, R₁ to R₈ in Formula 1 may all be identical to eachother.

In another embodiment, R₁ to R₈ in Formula 1 may each be independentlyhydrogen, deuterium, a halogen atom, a hydroxyl group, a cyano group, anitro group, a carboxyl group, a C₁-C₁₀ alkyl group, or a C₁-C₁₀ alkoxygroup, but are not limited thereto.

A weight average molecular weight of the polymer comprising a repeatingunit of Formula 1 may be about 2,000 Daltons to about 1,000,000 Daltons,based on polystyrene, but is not limited thereto, and a polydispersityindex (PDI) of the polymer may be about 1.5 to about 5 but is notlimited thereto. The weight average molecular weight and the PDI may bemeasured by, for example, gel permeation chromatography (GPC) based onpolystyrene, and may be appropriately determined by further considering,for example, the desired structure and characteristics of an organiclight-emitting device including the polymer.

As used herein, when a definition is not otherwise provided, the term“substituted X group” in the phrase “substituted or unsubstituted Xgroup” (where X is a defined group), used herein refers to replacementof one or more hydrogen atoms of the X group with a substituent selectedfrom deuterium, a halogen atom, a hydroxyl group, a nitro group, a cyanogroup, an amidino group, a hydrazinyl group, a carboxylic acid group ora salt thereof, a sulfonic acid group or a salt thereof, a phosphoricacid group or a salt thereof, a substituted or unsubstituted C₁-C₆₀alkyl group, a substituted or unsubstituted C₂-C₆₀ alkenyl group, asubstituted or unsubstituted C₂-C₆₀ alkynyl group, a substituted orunsubstituted C₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₆₀cycloalkyl group, a substituted or unsubstituted C₃-C₆₀ cycloalkenylgroup, a substituted or unsubstituted C₆-C₆₀ aryl group, a substitutedor unsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstitutedC₁-C₆₀ heteroaryl group, —N(Q₁₀₁)(Q₁₀₂), —Si(Q₁₀₃)(Q₁₀₄)(Q₁₀₅), and acombination thereof, wherein Q₁₀₁ to Q₁₀₅ may each be independentlyhydrogen, a halogen, a hydroxyl group, a cyano group, a nitro group, acarboxyl group, a substituted or unsubstituted C₁-C₆₀ alkyl group, asubstituted or unsubstituted C₂-C₆₀ alkenyl group, a substituted orunsubstituted C₂-C₆₀ alkynyl group, a substituted or unsubstitutedC₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₆₀ cycloalkylgroup, a substituted or unsubstituted C₃-C₆₀ cycloalkenyl group, asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstitutedC₆-C₆₀ arylthio group, or a substituted or unsubstituted C₁-C₆₀heteroaryl group. If there are two or more substituents, thesubstituents may be identical to or different from each other.

For example, the term “substituted X group” indicates replacement of oneor more hydrogen atoms of the X group with a substituent selected fromdeuterium, a halogen atom, a hydroxyl group, a cyano group, asubstituted or unsubstituted C₁-C₁₀ alkyl group, a substituted orunsubstituted C₁-C₁₀ alkoxy group, a substituted or unsubstituted C₆-C₂₀aryl group, a substituted or unsubstituted C₁-C₂₀ heteroaryl group,—N(Q₁₀₁)(Q₁₀₂), —Si(Q₁₀₃)(Q₁₀₄)(Q₁₀₅), and a combination thereof,wherein Q₁₀₁ to Q₁₀₅ may each be independently hydrogen, a halogen, ahydroxyl group, a cyano group, a substituted or unsubstituted C₁-C₁₀alkyl group, a substituted or unsubstituted C₁-C₁₀ alkoxy group, asubstituted or unsubstituted C₆-C₂₀ aryl group, or a substituted orunsubstituted C₁-C₂₀ heteroaryl group.

As another example, the term “substituted X group” indicates replacementof one or more hydrogen atoms of the X group with a substituent selectedfrom deuterium, a halogen atom, a hydroxyl group, a cyano group, aC₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, a C₆-C₂₀ aryl group, a C₁-C₂₀heteroaryl group, —N(Q₁₀₁)(Q₁₀₂), —Si(Q₁₀₃)(Q₁₀₄)(Q₁₀₅), and acombination thereof, wherein Q₁₀₁ to Q₁₀₅ may each be independentlyhydrogen, a halogen, a hydroxyl group, a cyano group, a C₁-C₁₀ alkylgroup, a C₁-C₁₀ alkoxy group, a C₆-C₂₀ aryl group, or a C₁-C₂₀heteroaryl group.

In still another example, the term “substituted X group” indicatesreplacement of one or more hydrogen atoms of the X group with asubstituent selected from deuterium, a halogen atom, a hydroxyl group, acyano group, a methyl group, an ethyl group, a propyl group, a butylgroup, a pentyl group, a methoxy group, an ethoxy group, a propoxygroup, a pentoxy group, a phenyl group, a naphthyl group, an anthrylgroup, and a combination thereof.

The “unsubstituted C₁-C₆₀ alkyl group” as used herein refers to astraight or branched chain saturated aliphatic hydrocarbyl group havingthe specified number of carbon atoms and a valence of one. Nonlimitingexamples thereof include methyl, ethyl, propyl, isobutyl, sec-butyl,pentyl, iso-amyl, hexyl, heptyl, octyl, and nonyl. The substitutedC₁-C₆₀ alkyl group may be substituted with one or more substituents asdescribed above where the term “substituted X group” is described indetail.

The term “unsubstituted C₂-C₆₀ alkenyl group” as used herein refers to astraight or branched chain hydrocarbyl group having the specified numberof carbon atoms, a valence of one, and at least one carbon-carbon doubleblond at the center or at a terminal of the unsubstituted C₂-C₆₀ alkylgroup. Nonlimiting examples of the unsubstituted C₂-C₆₀ alkenyl groupare ethenyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl,propadienyl, isoprenyl, and allyl. The substituted C₂-C₆₀ alkenyl groupmay be substituted, where indicated, with one or more substituentsdescribed above where the term “substituted X group” is described indetail.

The term “unsubstituted C₂-C₆₀ alkynyl group” as used herein refers to astraight or branched chain hydrocarbon chain having the specified numberof carbon atoms, a valence of one, and at least one carbon-carbon triplebond at the center or at a terminal of the unsubstituted C₂-C₆₀ alkylgroup. Nonlimiting examples of the unsubstituted C₂-C₆₀ alkynyl groupinclude acetylenyl, and the like. The substituted C₂-C₆₀ alkynyl groupmay be substituted, where indicated, with one or more substituentsdescribed above where the term “substituted X group” is described indetail.

The term “unsubstituted C₁-C₆₀ alkoxy group” as used herein has aformula represented by —OY where Y is the unsubstituted C₁-C₆₀ alkylgroup as defined above. Nonlimiting examples of the unsubstituted C₁-C₆₀alkoxy group include methoxy, ethoxy, isopropyloxy, butoxy, and pentoxy.The substituted C₁-C₆₀ alkoxy group may be substituted, where indicated,with one or more substituents described above where the term“substituted X group” is described in detail.

The term “unsubstituted C₃-C₆₀ cyclo alkyl group” as used herein refersto a hydrocarbyl group having one or more cyclic saturated rings inwhich all ring members are carbon, the specified number of carbon atoms,and a valence of one. Nonlimiting examples of the unsubstituted C₃-C₆₀cyclo alkyl group include cyclopropyl, cyclobutyl, cyclopentyl,cyclohexyl, cycloheptyl, cyclooctyl, and adamantyl groups. Thesubstituted C₁-C₆₀ cycloalkyl group may be substituted, where indicated,with one or more substituents described above where the term“substituted X group” is described in detail.

The term “unsubstituted C₃-C₆₀ cycloalkenyl group” as used herein refersto a cycloalkyl group having at least one carbon-carbon double bond inthe ring. Nonlimiting examples of the unsubstituted C₃-C₆₀ cyclo alkenylgroup include cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl,cycloheptenyl, 1,3-cyclohexadienyl, 1,4-cyclohexadienyl,2,4-cycloheptadienyl, and 1,5-cyclooctadienyl. A “C₃-C₆₀ cycloalkynyl”group is a cycloalkyl group having at least one carbon-carbon triplebond in the ring. The cycloalkenyl and cycloalkynyl groups do notcontain an aromatic ring or a heterocyclic ring. The substituted C₃-C₆₀cyclo alkenyl and cycloalkynyl groups may be substituted, whereindicated, with one or more substituents described above where the term“substituted X group” is described in detail.

The term “unsubstituted C₃-C₆₀ alkylene” group refers to an alkyl grouphaving the specified number of carbon atoms, a valence of two or higher,and may be optionally substituted, where indicated, with one or moresubstituents described above where the term “substituted X group” isdescribed in detail.

The term “unsubstituted C₆-C₆₀ aryl group” as used herein refers to amonovalent group having a carbocyclic aromatic system in which thenumber of carbon atoms is 6 to 60, and may be a monocyclic group or apolycyclic group. If the unsubstituted C₆-C₆₀ aryl group is a polycyclicgroup, two or more ring may be present, and any additional rings may beindependently aromatic, saturated, or partially unsaturated and multiplerings, if present, may be fused, pendent, spirocyclic or a combinationthereof. Nonlimiting examples of the unsubstituted C₆-C₆₀ aryl groupinclude phenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl,indacenyl, acenaphthyl, fluorenyl, spiro-fluorenyl, phenalenyl,phenanthryl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl,naphthacenyl, picenyl, perylenyl, pentaphenyl, hexacenyl, andtetrahydronaphthyl groups. The substituted C₆-C₆₀ aryl group may be oneor more substituents described above where the term “substituted Xgroup” is described in detail.

The term “unsubstituted C₆-C₆₀ arylene group” as used herein refers to adivalent group having a carbocyclic aromatic system in which thespecified number of carbon atoms is 6 to 60, wherein the points ofattachment may be on the same or different rings, each of which ringsmay be aromatic or nonaromatic. Nonlimiting examples of theunsubstituted C₆-C₆₀ arylene group include phenylene and naphthylene.The substituted C₆-C₆₀ arylene group may be substituted with one or moresubstituents described above where the term “substituted X group” isdescribed in detail.

The term “unsubstituted C₆-C₆₀ aryloxy” group” as used herein has aformula represented by —OY where Y is the unsubstituted C₁-C₆₀ arylgroup as defined above. Nonlimiting examples of the unsubstituted C₁-C₆₀alkoxy group include phenoxy. The substituted C₆-C₆₀ arylalkoxy groupmay be substituted, where indicated, with one or more substituentsdescribed above where the term “substituted X group” is described indetail.

The term “unsubstituted C₆-C₆₀ arylthio” group” as used herein has aformula represented by —SY where Y is the unsubstituted C₁-C₆₀ arylgroup as defined above. The substituted C₆-C₆₀ arylalkoxy group may besubstituted, where indicated, with one or more substituents describedabove where the term “substituted X group” is described in detail.

The term “unsubstituted C₁-C₆₀ heteroaryl group” as used herein refersto a monocyclic or polycyclic group, each having at least one ringhaving one or more heteroatoms in the ring independently selected fromnitrogen (N), oxygen (O), phosphorous (P), sulfur (S), and a combinationthereof. If the unsubstituted C₂-C₆₀ hetero aryl group is a polycyclicgroup, two or more rings contained in the unsubstituted C₂-C₆₀heteroaryl group may be present, and any additional rings may beindependently aromatic, saturated, or partially unsaturated and multiplerings, if present, may be fused, pendent, spirocyclic or a combinationthereof. Nonlimiting examples of the unsubstituted C₂-C₆₀ heteroarylgroup include pyrrolyl, imidazolyl, pyrazolyl, pyridinyl, pyrazinyl,pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl,quinolinyl, benzoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl,quinazolinyl, cinnolinyl, carbazolyl, phenanthridinyl, acridinyl,phenanthrolinyl, phenazinyl, benzooxazolyl, benzoimidazolyl, furanyl,benzofuranyl, thiophenyl, benzothiophenyl, thiazolyl, isothiazolyl,benzothiazolyl, isoxazolyl, oxazolyl, triazolyl, tetrazolyl,oxadiazolyl, triazinyl, and benzooxazolyl. The substituted C₆-C₆₀heteroaryl group may be substituted with one or more substituentsdescribed above where the term “substituted X group” is described indetail.

The term “unsubstituted C₆-C₆₀ heteroarylene group” as used hereinrefers to a divalent monocyclic or polycyclic group having at least onering having one or more hetero atoms in the ring independently selectedfrom nitrogen (N), oxygen (O), phosphorous (P), and sulfur (S).Nonlimiting examples of the unsubstituted C₆-C₆₀ heteroarylene group maybe understood by referring to the examples of the unsubstituted C₆-C₆₀heteroaryl group above. The substituted C₆-C₆₀ heteroarylene group maybe substituted with one or more substituents described above where theterm “substituted X group” is described in detail.

The expression “*” used herein refers to a binding site with an adjacentmoiety, including for example, a point of attachment of each repeat unitof a polymer.

According to an embodiment, the polymer including the repeating unitrepresented by Formula 1 may be synthesized using a known organicsynthesis method, for example, Suzuki coupling or Yamamoto coupling. Thesynthesis methods are known to one of ordinary skill in the art withreference to examples which will be presented later.

The polymer having the repeating unit represented by Formula 1 is abipolar polymer having an electron transporting part represented by Eand a hole transporting part represented by H in a main backbone, asillustrated in Formula 1-2 shown in FIG. 6,

wherein the variables have the same definitions as described above inFormula 1. The polymer of Formula 1-2 is formed by connecting two of therepeating units represented by Formula 1. Due to the inclusion of theelectron transporting part and the hole transporting part, a balancebetween hole transport and electron transport may be effectively madeand maintained.

Also, without being bound by theory, linking between positions 3 and 6in benzene rings of the hole transporting part H may contribute tomaintenance of an energy band gap (Eg) and triplet energy (E_(T)) athigh levels even when a conjugation length of the polymer is increased.

Also, since a conjugation length of the polymer may be easily adjustedby controlling the variable m, in the polymer, hole and electroninjection and transport characteristics of the polymer may be optimizedaccording to a moiety of the hole transporting part H.

Accordingly, the polymer comprising unites represented by Formula 1, maybe used in an organic light-emitting device, for example, as aphosphorescent host, which is used together with a phosphorescent dopantin an emitting layer of an organic light-emitting device.

Unlike a fluorescent material having a maximum internal quantumefficiency of 25% in which only singlet state energy contributes tolight-emission, a phosphorescent material that enables intersystemcrossing between singlet state energy and triplet state energy has, intheory, a maximum internal quantum efficiency of 100% since excitonshaving triplet state energy also contribute to light-emission.Accordingly, an organic light-emitting device including a phosphorescentmaterial has high efficiency. If a high level of triplet state energy ofa known phosphorescent dopant and characteristics of the polymerdescribed above are taken into consideration, the polymer is suitablefor use as a phosphorescent host in an emitting layer of an organiclight-emitting device.

For example, the polymer may be used as a red, green, and/or bluephosphorescent host in an emitting layer of an organic light-emittingdevice. According to an embodiment, the polymer may be used as a redand/or green phosphorescent host in an emitting layer of an organiclight-emitting device, but is not limited thereto.

Accordingly, provided is an organic light-emitting device including asubstrate; a first electrode; a second electrode; and a first layer thatis disposed between the first electrode and the second electrode andincludes the polymer including the repeating unit represented by Formula1.

The first layer of the organic light-emitting device may function, forexample, as an emitting layer.

If the first layer is an emitting layer, the first layer may furtherinclude a phosphorescent dopant. The phosphorescent dopant may be anyone of known phosphorescent dopants. For example, the phosphorescentdopant may be an organometallic complex including iridium (Ir), platinum(Pt), osmium (Os), rhenium (Re), titanium (Ti), zirconium (Zr), hafnium(Hf), or a combination thereof, but is not limited thereto.

Nonlimiting examples of the phosphorescent dopant include the metalliccompound coupled to a combination of groups selected from a substitutedor unsubstituted acetylacetonate group, a substituted or unsubstitutedheteroaryl(heteroaryl) group, a substituted or unsubstitutedbiaryl(heteroaryl) group, a substituted or unsubstituted biheteroarylgroup, a substituted or unsubstituted aryl(heterocycloalkyl) group, asubstituted or unsubstituted aryl(heteroaryl) group, a substituted orunsubstituted alkylporphyrin group, a substituted or unsubstitutedarylisoquinoline group, a substituted or unsubstituted arylquinolinegroup, a substituted or unsubstituted picolinate group, a substituted orunsubstituted heterocycloalkyl(heteroaryl) group, and the like. Morespecifically, nonlimiting examples of the phosphorescent dopant includebisthienylpyridine acetylacetonate iridium,bis(benzothienylpyridine)acetylacetonate iridium,bis(2-phenylbenzothiazole)acetylacetonate iridium,bis(1-phenylisoquinoline) iridium acetylacetonate,tris(1-phenylisoquinoline) iridium, tris(phenylpyridine) iridium,tris(2-biphenylpyridine) iridium, tris(3-biphenylpyridine) iridium,tris(4-biphenylpyridine) iridium, Pq₂Ir(acac) where pq is anabbreviation of 2-phenylquinoline and acac is an abbreviation ofacetylacetone (Compound 10), Ir(ppy)₃ where ppy is an abbreviation ofphenylpyridine (Compound 11), Ir(2′,6′-difluoro-2,3′-bipyridine)₃(Compound 12), Firpic(Bis(4,6-difluorophenylpyridinato-N,C2)picolinatoiridium) (Compound 13),Ir (piq)₂acac where piq is an abbreviation of phenylisoquinoline(Compound 14), Ir(mppy)₃ where mppy is an abbreviation ofmethylphenylpyridine (see Compound 15 blow),platinum(II)octaethylporphyrin (PtOEP) (Compound 16), Ir(piq)₃ (Compound17), Btp₂Ir(acac) where Btp is an abbreviation of benzothienylpyridine(Compound 18), F₂Irpic(bis[2-(4,6-difluorophenyl)pyridinato-N,C2′]iridium picolinate)(Compound 19 (F₂ ppy)₂Ir(tmd) where tmd is an abbreviation oftetramethyldione (Compound 20), Ir(dfppz)₃(tris[1-(4,6-difluorophenyl)pyrazolate-N,C2′]iridium) (Compound 21), anda combination thereof:

In addition to the first layer (functioning as, for example, an emittinglayer), a hole injection layer, a hole transport layer, a hole blockinglayer, an electron transport layer, an electron injection layer, or anycombination thereof may be further disposed between the first electrodeand the second electrode of the organic light-emitting device.

FIG. 1 is a schematic sectional view of an organic light-emitting device10 according to an embodiment. The organic light-emitting device 10includes a substrate 11, a first electrode 12, a hole transport layer13, a first layer 15, an electron transport layer 16, an electroninjection layer 18, and a second electrode 19. The first layer 15 mayfunction as an emitting layer. The organic light-emitting device 10 anda method of manufacturing the organic light-emitting device 10 will nowbe described in detail.

First, a first electrode material having a high work function may bedisposed, deposited, ion-plated, plated, or sputtered on the substrate11 to form the first electrode 12. The first electrode 12 may be ananode through which holes are injected or a cathode through whichelectrons are injected. The substrate 11 may be any one of varioussubstrates that are used in a known organic light-emitting device, andmay be a glass substrate or a transparent plastic substrate havingexcellent mechanical strength, thermal stability, transparency, surfacesmoothness, ease of handling, and water repellence. The first electrodematerial may be a metal oxide, a metal sulfide, or a metal, each ofwhich has high electrical conductivity, and in general, these materialsmay be used as a thin film. The first electrode material may also be apolyaryl based or polyheteroaryl based material. More specifically,nonlimiting examples of the first electrode material include an oxidesuch as an indium oxide, a zinc oxide, a tin oxide, an indium tin oxide(ITO), or an indium zinc oxide (IZO), gold, platinum, silver, andcopper. The first electrode material may also be polyaniline or aderivative thereof, polythiophene or a derivative thereof, and the like.The first electrode 12 may have a one-layer structure or a multi-layerstructure including two or more layers, and may include two or moredifferent materials. A thickness of the first electrode 12 may beappropriately controlled by considering transmissivity of light andelectrical conductivity, and may be, for example, about 10 nanometers(nm) to about 10 micrometers (μm).

Although not illustrated in FIG. 1, according to another embodiment, ifthe first electrode 12 is an anode, a hole injection layer may befurther disposed, e.g., formed on the first electrode 12. The holeinjection layer may be disposed, e.g., formed on the first electrode 12by using any one of various methods, for example, vacuum deposition,spin coating, casting, or Langmuir-Blodgett (LB) deposition.

When the hole injection layer is formed on the first electrode 12 byvacuum deposition, the deposition conditions may vary according to amaterial that is used to form the hole injection layer, and thestructure and thermal characteristics of the hole injection layer. Forexample, the deposition conditions may include a deposition temperatureof about 100° C. to about 500° C., a vacuum pressure of about 10⁻⁸ torrto about 10⁻³ torr, and a deposition rate of about 0.01 Angstrom/secondto about 100 Angstrom/second.

When the hole injection layer is formed on the first electrode 12 usingspin coating, coating conditions may vary according to the material usedto form the hole injection layer, and the structure and thermalproperties of the hole injection layer. For example, the coatingconditions may include a coating speed of about 2000 revolutions perminute (rpm) to about 5000 rpm, and a heat treatment temperature ofabout 80° C. to about 300° C., wherein the heat treatment serves toremove the solvent after coating.

A material that is used to form the hole injection layer may be any oneof known hole injecting materials. Nonlimiting examples of the materialinclude a substituted or unsubstituted phthalocyanine compound, asubstituted or unsubstituted bis(triarylamino) compound, an amino groupcoupled to at least one substituted or unsubstituted triarylamino group,and the like. More specifically, nonlimiting examples of the materialinclude copper phthalocyanine,4,4′,4″-tris(3-methylphenylphenylamino)triphenylamine (m-MTDATA) whoseformula is presented below, N,N′-di(1-naphthyl)-N,N′-diphenylbenzidine(NPB),N¹,N¹-bis(4-(diphenylamino)phenyl)-N⁴,N⁴-diphenylbenzene-1,4-diamine(TDATA) whose formula is presented below,N¹-(naphthalen-2-yl)-N⁴,N⁴-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N¹-phenylbenzene-1,4-diamine(2T-NATA) having the formula below, and the like.

The hole injection layer may have a thickness of about 100 nm to about10000 nm. More specifically the hole injection layer may have, forexample, a thickness of about 100 nm to about 1000 nm. When thethickness of the hole injection layer is within these ranges, the holeinjection layer may have good hole injection characteristics without anincrease in driving voltage.

The hole transport layer 13 may be disposed, e.g., formed on the firstelectrode 12 or the hole injection layer by vacuum deposition, spincoating, casting, LB deposition, and the like.

When the hole transport layer 13 is disposed, e.g., formed on the firstelectrode 12 by vacuum deposition or spin coating, the deposition orcoating conditions may be similar to those applied to form the holeinjection layer, although the deposition or coating conditions may varyaccording to the material that is used to form the hole transport layer.

A material that is used to form the hole transport layer 13 may be anyone of known hole transport materials. Nonlimiting examples of thematerial that is used to form the hole transport layer 13 include asubstituted or unsubstituted bis(triarylamino) based compound, asubstituted or unsubstituted polyaniline/substituted or unsubstitutedarylsulfonic acid group, a substituted or unsubstitutedpolyaniline/substituted or unsubstituted cycloalkylsulfonic acid groupwherein the cycloalkyl group may be a substituted or unsubstitutedbridged cycloalkyl group, a substituted or unsubstitutedpolyaniline/substituted or unsubstituted polystyrenesulfonic acid group,a substituted or unsubstituted polyheteroaryl/substituted orunsubstituted polystyrenesulfonic acid group and the like. Morespecifically, nonlimiting examples of the material that is used to formthe hole transport layer 13 includeN,N′-bis(3-methylphenyl)-N,N′-diphenyl-[1,1-biphenyl]-4,4′-diamine (TPD)whose formula is presented below, polyaniline/dodecylbenzenesulfonicacid (Pani/DBSA) a polymer with a repeating unit represented by theformula below, poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate)(PEDOT/PSS) a polymer with a repeating unit represented by the formulabelow, polyaniline/camphor sulfonic acid (Pani/CSA) a polymer with arepeating unit represented by the formula below,polyaniline/poly(4-styrenesulfonate) (Pani/PSS) a polymer with arepeating unit represented by the formula below, and the like.

The hole transport layer 13 may have a thickness of about 50 nm to about1000 nm. More specifically, the hole transport layer 13 may have, forexample, a thickness of about 100 nm to about 600 nm. When the thicknessof the hole transport layer 13 is within the above range, the holetransport layer 13 may have excellent hole transport characteristicswithout an increase in driving voltage.

The first layer 15 that may function as an emitting layer, may bedisposed on the hole transport layer 13. The first layer 15 may bedisposed on the hole transport layer 13 by spin coating, casting, LBdeposition, and the like. If the first layer 15 is disposed on the holetransport layer 13 by spin coating, the coating conditions may besimilar to those used to dispose the hole injection layer on the firstelectrode 12, although the coating conditions may vary according to thepolymer and/or compound that is used to form the first layer 15.

The first layer 15 may include the polymer having the repeating unitrepresented by Formula 1 as a host. Also, the first layer 15 may furtherinclude a phosphorescent dopant, in addition to the polymer having therepeating unit represented by Formula 1. Examples of the phosphorescentdopant have already been described above.

If the first layer 15 includes the polymer having the repeating unitrepresented by Formula 1 and a phosphorescent dopant, an amount of thephosphorescent dopant contained in the first layer 15 may be about 1 wt.% to about 10 wt. % based on 100 wt. % of the total weight of the firstlayer 15. If the amount of the phosphorescent dopant is within theranges described above, concentration quenching may be substantiallyprevented.

The first layer 15 may include only the polymer having the repeatingunit represented by Formula 1. Alternatively, the first layer 15 mayinclude the polymer having the repeating unit represented by Formula 1and a known fluorescent dopant, but is not limited thereto.

A thickness of the first layer 15 that functions as an emitting layermay be about 100 nm to about 1000 nm, and more specifically, about 200nm to about 900 nm. If the thickness of the first layer 15 is withinthese ranges, the first layer 15 may have good light-emittingcharacteristics without an increase in driving voltage.

Although not illustrated in FIG. 1, according to another embodiment, ahole blocking layer may be further disposed on the first layer 15.

The hole blocking layer may prevent diffusion of triplet excitons orholes in the first layer 15 that functions as an emitting layer to thesecond electrode 19. The hole blocking layer may be disposed, e.g.,formed on the first layer 15 by vacuum deposition, spin coating,casting, LB deposition, and the like. If the hole blocking layer isformed on the first layer 15 by vacuum deposition or spin coating, thedeposition or coating conditions may be similar to those applied to formthe hole injection layer on the first electrode 12, although thedeposition or coating conditions may vary according to the material thatis used to form the hole blocking layer. Nonlimiting examples of a knownhole blocking material include an oxadiazole derivative, a triazolederivative, a phenanthroline derivative, a pyridazine derivative, andthe like. More specifically, nonlimiting examples of a known holeblocking material include pyridazine[1,2-a]cinnoline whose formula ispresented below, and 4-(naphthalen-1-yl)-3,5-diphenyl-4H-1,2,4-triazole(TAZ) whose formula is presented below, and the like.

A thickness of the hole blocking layer may be about 50 nm to about 1000nm, and more specifically, about 100 nm to about 300 nm. If thethickness of the hole blocking layer is within these ranges, the holeblocking layer may have satisfactory hole blocking characteristics.

Next, the electron transport layer 16 is disposed on the first layer 15or the hole blocking layer, by vacuum deposition, spin coating, casting,and the like. If the electron transport layer 16 is disposed on thefirst layer 15 by vacuum deposition or spin coating, the deposition orcoating conditions may be similar to those applied to dispose the holeinjection layer on the first electrode 12, although the deposition orcoating conditions may vary according to the material that is used toform the electron transport layer 16.

A material that is used to form the electron transport layer 16 may be amaterial that stably transports electrons injected through an electrodeinjection electrode (cathode). Nonlimiting examples of the material thatis used to form the electron transport layer 16 include a substituted orunsubstituted phenanthroline compound; a substituted or unsubstitutedbenzoimidazole compound; a metallic compound coupled via an etherlinkage to a combination of groups selected from a substituted orunsubstituted quinoline group, a substituted or unsubstituted biarylgroup, and a substituted or unsubstituted benzoquinoline group; and thelike. More specifically, nonlimiting examples of the material that isused to form the electron transport layer include4,7-diphenyl-1,10-phenanthroline (Bphen), BAIq where B is anabbreviation of biphenyl and q is an abbreviation of a quinoline groupwhose formula is presented below, tris(8-quinolinorate)aluminum (Alq3),beryllium bis(benzoquinolin-10-olate) (Bebq₂),1,3,5-tris(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBi) whoseformula is presented below, and the like.

The electron transport layer 16 may have a thickness of about 100 nm toabout 1,000 nm, and more specifically, about 200 nm to about 500 nm. Ifthe thickness of the electron transport layer 16 is within these ranges,the electron transport layer 16 may have good electron transportcharacteristics without an increase in driving voltage.

Subsequently, the electron injection layer 18 may be disposed on theelectron transport layer 16. A material that is used to form theelectron injection layer 18 may be any one of known materials that areused to form an electron injection layer, and may be a metal halide or ametal oxide. More specifically, nonlimiting examples of the materialused to form the electron injection layer 18 include lithium fluoride(LiF), sodium chloride (NaCl), cesium fluoride (CsF), lithium oxide(Li₂O), barium oxide (BaO), or barium fluoride (BaF₂). The depositionconditions may be similar to those applied to dispose the hole injectionlayer on the first electrode 12, although the deposition conditions mayvary according to the material that is used to form the electroninjection layer 18.

The electron injection layer 18 may have a thickness of about 1 nm to100 nm, and more specifically, about 5 nm to about 50 nm. When thethickness of the electron injection layer 18 is within these ranges, theelectron injection layer 18 may have good electron injectioncharacteristics without an increase in driving voltage.

Finally, the second electrode 19 may be disposed, e.g., formed on theelectron injection layer 18. A method of forming the second electrode 19on the electron injection layer 18 may be understood by referring to themethod of forming the first electrode 12 on the substrate 11 asdescribed above. The second electrode 19 may be used as a cathode or ananode. If the second electrode 19 is used as a cathode, the secondelectrode 19 may be formed of a material having a low work function.Nonlimiting examples of the low work function material include graphite;a graphite interlayer compound; an alkali metal, an alkali earth metal,and a metal; an alloy comprising at least two elements selected from analkali metal, an alkali earth metal and a metal; and an alloy comprisingat least one alkali metal, an alkali earth metal, and a metal, and atleast one transition metal, an actinide and a poor metal element. Morespecifically, nonlimiting examples of the low work function materialinclude lithium; sodium; potassium; rubidium; cesium; beryllium;magnesium; calcium; strontium; barium; aluminum; scandium; vanadium;zinc; yttrium; indium; cerium; samarium; europium; terbium; ytterbium;an alloy comprising at least two elements selected from lithium, sodium,potassium, rubidium, cesium, beryllium, magnesium, calcium, strontium,barium, aluminum, scandium, vanadium, zinc, yttrium, indium, cerium,samarium, europium, terbium, and ytterbium; an alloy comprising at leastone element selected from lithium, sodium, potassium, rubidium, cesium,beryllium, magnesium, calcium, strontium, barium, aluminum, scandium,vanadium, zinc, yttrium, indium, cerium, samarium, europium, terbium,and ytterbium, and at least one element selected from gold, silver,plutonium, copper, manganese, titanium, cobalt, nickel, tungsten, andtin; graphite; a graphite interlayer compound; and the like. Morespecific nonlimiting examples of the alloys include a magnesium-silveralloy, a magnesium-indium alloy, a magnesium-aluminum alloy, anindium-silver alloy, a lithium-aluminum alloy, a lithium-magnesiumalloy, a lithium-indium alloy, and a calcium-aluminum alloy. Also, thesecond electrode 19 may have a one-layer structure or a multi-layerstructure. Also, the second electrode 19 may include only one kind ofmaterial, or two or more different materials. The second electrode 19may be a transparent, semi-transparent, or reflective electrode. Athickness of the second electrode 19 may be, for example, about 10 nm toabout 10 μm, but is not limited thereto.

One or more embodiments will now be described in further detail withreference to the following examples. These examples are for illustrativepurposes only and are not intended to limit the scope of the one or moreembodiments.

Synthesis Example 1 Synthesis of Compound 1

Compound 1 was synthesized according to Reaction Scheme 1 below.

Synthesis of Intermediate 1

17.9 grams (g) (129 millimoles (mmole)) of potassium carbonate (K₂CO₃)was added to 14.9 g (86.2 mmole) of 4-bromophenol in 200 milliliters(mL) of acetone and the mixture was heated at a refluxing temperature.After 30 minutes, 24 mL (129 mmole) of 2-ethylhexyl bromide was droppedinto the reaction mixture. After a reaction was completed, the reactionmixture was cooled to room temperature, washed with brine, extractedwith methylene chloride (CH₂Cl₂), dried with anhydrous magnesium sulfate(MgSO₄), filtered, and concentrated under reduced pressure. The residualwas refined by using column chromatography to obtain 23.3 g ofIntermediate 1 (1-bromo-4-((2-ethylhexyl)oxy)benzene) (Yield: 97%).

¹H-NMR (deuterated chloroform (CDCl₃), 300 MegaHertz (MHz)): δ 7.40-7.37(d, 2H), 6.82, 6.79 (d, 2H), 3.84-3.82 (d, 2H), 1.74 (m, 1H), 1.57-1.34(m, 10H), 0.98-0.84 (m, 6H)

¹³C-NMR (CDCl₃, 75 MHz): δ 158.5, 132.1, 116.3, 112.4, 70.7, 39.3, 30.5,28.8, 25.1, 23.8, 14.1, 11.6

Synthesis of Intermediate 2

In a nitrogen atmosphere, 16.8 g (49.2 mmole) of Intermediate 1 in 20 mLof dimethylformamide (DMF) was dropped into 8.6 g (49.2 mmole) ofcarbazole, 281 milligrams (mg) (1.5 mmole) of copper iodide (CuI), 541mg (3.0 mmole) of 1,10-phenanthroline, and 13.6 g (98.4 mmole) of K₂CO₃in 100 mL of DMF, and the mixture was heated at a temperature of 155° C.and stirred for 24 hours. After a reaction was completed, the reactionmixture was filtered with a celite pad, and washed with CH₂Cl₂. Thefiltrate was washed with brine and dried with anhydrous MgSO₄, filtered,and concentrated under reduced pressure. The residual was refined byusing column chromatography to obtain 12.2 g of Intermediate 2(9-(4-((2-ethylhexyl)oxy)phenyl)-9H-carbazole) (67%).

¹H-NMR (CDCl₃, 300 MHz): δ 8.17 (d, 2H), 7.49-7.12 (m, 8H), 7.11 (d,2H), 3.99 (d, 2H), 1.86-1.82 (m, 1H), 1.80-1.42 (m, 8H), 1.08-0.94 (m,6H)

¹³C-NMR (CDCl₃, 75 MHz): δ 158.7, 141.4, 130.0, 128.5, 125.8, 123.0,120.2, 119.6, 115.6, 109.7, 70.8, 39.4, 30.6, 29.1, 23.9, 23.1, 14.1,11.1

Synthesis of Intermediate 3

7.7 g (43 mL) of N-bromosuccinimide (NBS) was dropped into 8.0 g (21.5mmole) of Intermediate 2 in 50 mL of a mixture including (chloroform)CHCl₃ and DMF (a volumetric ratio of CHCl₃ to DMF was 3:1), and areaction was performed at room temperature. After the reaction wascompleted, the reaction mixture was washed with brine, extracted withCH₂Cl₂, dried with anhydrous MgSO₄, filtered, and concentrated underreduced pressure. The residual was refined by using columnchromatography to obtain 10.4 g of Intermediate 3(3,6-dibromo-9-(4-((2-ethylhexyl)oxy)phenyl)-9H-carbazole) (Yield: 94%).

¹H-NMR (CDCl₃, 300 MHz): δ 8.20 (s, 2H), 7.51-7.48 (d, 2H), 7.37-7.32(d, 2H), 7.20-7.08 (dd, 4H), 3.98 (d, 2H), 1.84 (m, 1H), 1.80-1.40 (m,8H), 1.09-0.93 (m, 6H)

¹³C-NMR (CDCl₃, 75 MHz): δ 159.1, 140.3, 129.2, 128.9, 128.3, 123.6,123.1, 115.7, 112.7, 111.4, 70.9, 39.4, 30.5, 29.1, 23.9, 23.1, 14.1,11.1

Synthesis of Compound 1

6.09 g (23.5 mmole) of bis(pinacolato)diboron was added to 5 g (9.4mmole) of Intermediate 3, 154 mg (0.188 mmole) ofdichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II)(PdCl₂(dppf), 107 mg (0.188 mmole) ofdppf(1,1′-bis(diphenylphosphino)-ferrocene), and 5.6 g (56.4 mmole) ofpotassium acetate (KOAc) in 20 mL of 1,4-dioxane, and the resultantmixture was heated until the temperature reached 100° C. and stirred for24 hours in a nitrogen atmosphere. After a reaction was completed, thereaction mixture was filtered with a celite pad and washed with CH₂Cl₂.The filtrate was washed with brine, dried with anhydrous MgSO₄,filtered, and concentrated under reduced pressure. The residual wasrefined by using column chromatography to obtain 23.3 g of Compound 1(9-(4-((2-ethylhexyl)oxy)phenyl)-3,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole)(Yield: 97%)

¹H-NMR (CDCl₃, 300 MHz): δ 8.73 (s, 2H), 7.82 (d, 2H), 7.41 (d, 2H),7.25 (d, 2H), 7.09 (d, 2H), 3.98 (d, 2H), 1.79 (m, 1H), 1.65-1.27 (m,34H), 0.98 (m, 6H)

Synthesis Example 2 Synthesis of Compound 2

Compound 2 was synthesized according to Reaction Scheme 2 below.

Synthesis of Intermediate 5

In a nitrogen atmosphere, 1.9 g (11.7 mmole) of iron chloride (FeCl₃)was added to 2.2 g (5.9 mmole) of Intermediate 2 stirred in 50 mL ofCHCl₃. After a reaction was completed, water (H₂O) was added to thereaction mixture. An organic layer was isolated and dried with anhydrousMgSO₄, filtered, and concentrated under reduced pressure. The residualwas refined by using column chromatography and re-crystallized using ahexane medium to obtain 1.0 g of Intermediate 5(9,9′-bis(4-((2-ethylhexyl)oxy)phenyl)-9H,9′H-3,3′-bicarbazole) (Yield:47%)

¹H-NMR (CDCl₃, 300 MHz): δ 8.57 (s, 2H), 8.27 (d, 2H), 7.83 (d, 2H),7.54-7.28 (m, 12H), 7.19-7.16 (d, 4H), 4.01-3.99 (d, 4H), 1.88-1.84 (m,2H), 1.64-1.44 (m, 20H), 1.08-0.99 (m, 12H)

¹³C-NMR (CDCl₃, 75 MHz): δ 158.7, 141.8, 140.5, 134.2, 130.0, 128.4,125.9, 125.8, 123.7, 123.3, 120.4, 119.7, 118.8, 115.6, 109.9, 109.8,70.8, 39.5, 30.6, 29.1, 23.9, 23.1, 14.1, 11.2

Synthesis of Intermediate 6

498 mg (2.8 mmole) of NBS was dropped into Intermediate 5 in 1.0 g (1.4mmole) of a mixture including CHCl₃ and DMF (a volumetric ratio of CHCl₃to DMF is 3:1), and a reaction was performed at room temperature. Afterthe reaction was completed, the reaction mixture was washed with brine,extracted with CH₂Cl₂, dried with anhydrous MgSO₄, filtered, andconcentrated under reduced pressure. The residual was refined by usingcolumn chromatography to obtain 1.2 g of Intermediate 6(6,6′-dibromo-9,9′-bis(4-((2-ethylhexyl)oxy)phenyl)-9H,9′H-3,3′-bicarbazole)(Yield: 93%).

Synthesis of Compound 2

881 mg (3.4 mmole) of bis(pinacolato)diboron was added to 1.2 g (1.36mmole) of Intermediate 6, 22 mg (0.0272 mmole) of1,1′-bis(diphenylphosphino)ferrocene-palladium(II) dichloridedichloromethane (PdCl₂(dppf).CH₂Cl₂), 16 mg (0.0272 mmole) of dppf, and809 mg (8.16 mmole) of potassium acetate (KOAc) in 30 mL of 1,4-dioxane,and the reaction mixture was heated until the temperature reached 100°C. and stirred for 24 hours in a nitrogen atmosphere. After a reactionwas completed, the reaction mixture was filtered with a celite pad andwashed with CH₂Cl₂. The filtrate was washed with brine, dried withanhydrous MgSO₄, filtered, and concentrated under reduced pressure. Theresidual was refined by using column chromatography to obtain 1.0 g ofCompound 2(9,9′-bis(4-((2-ethylhexyl)oxy)phenyl)-6,6′-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H,9′H-3,3′-bicarbazole)(Yield: 75%).

¹H-NMR (CDCl₃, 300 MHz): δ 8.37-8.36 (d, 4H), 7.79-7.76 (d, 2H),7.53-7.50 (d, 2H), 7.47-7.41 (m, 6H), 7.28-7.16 (d, 2H), 7.13 (d, 4H),3.99 (d, 4H), 1.86 (m, 2H), 1.80-1.41 (m, 20H), 1.08-0.98 (m, 12H)

¹³C-NMR (CDCl₃, 75 MHz): δ 158.9, 140.8, 140.5, 134.2, 129.5, 128.6,128.3, 126.3, 125.0, 123.1, 122.6, 118.9, 115.7, 112.5, 111.3, 110.2,70.9, 39.4, 30.6, 29.1, 23.9, 23.1, 14.1, 11.2

Synthesis Example 3 Synthesis of Compound 3

Compound 3 was synthesized according to Reaction Scheme 3 below.

Synthesis of Intermediate 7

30 mL (263.2 mmole) of 2-chloro-2-methylpropane was dropped into asolution including 15.3 g (87.7 mmole) of carbazole and 36.6 g (263.2mmole) of zinc chloride (ZnCl₂) in a nitrogen atmosphere while stirring.After the mixture was stirred at a temperature of 40° C., it was addedto H₂O. The product was extracted with CH₂Cl₂, dried with MgSO₄,filtered, and concentrated under reduced pressure to obtain 23 g ofIntermediate 7 (Yield 94%), which was in the form of a white solid.

¹H NMR (CDCl₃, 300 MHz): δ 8.07 (d, 2H), 7.83 (b, 1H), 7.49 (dd, 2H),7.33 (dd, 2H), 1.44 (s, 18H).

Synthesis of Intermediate 9

In a nitrogen atmosphere, 10 g (35.8 mmole) of Intermediate 7, 20 g(71.6 mole) of Intermediate 8 (obtained from Aldrich Company), 205 mg(1.1 mmole) of copper iodide (CuI), 400 mg (2.2 mmole) of1,10-phenanthroline, and 7.4 g (53.7 mmole) of K₂CO₃ in 100 mL of DMFwere heated until the temperature reached 155° C. and the mixture wasstirred for 24 hours. After a reaction was completed, the reactionmixture was filtered with a celite pad and washed with CH₂Cl₂. Thefiltrate was washed with brine, dried with anhydrous MgSO₄, filtered,and concentrated under reduced pressure. The residual was refined byusing column chromatography to obtain Intermediate9(9-(4-((2-ethylhexyl)oxy)phenyl)-9H-carbazole) (9.6 g, 62%).

Synthesis of Intermediate 11

15 mL (23.98 mmole) of n-butyllithium (n-BuLi) was dropped into 9.5 g(21.87 mmole) of Intermediate 9 in 60 mL of tetrahydrofuran (THF) at atemperature of −78° C. After 30 minutes, 8.1 g (43.74 mmole) ofIntermediate 10 (obtained from Aldrich Company) in 40 mL of THF wasadded to the reaction mixture. The resultant mixture was placed in acooling bath overnight so that the temperature decreased to roomtemperature. After a reaction was completed, the reaction was quenchedusing H₂O, and the solvent was removed by evaporation under reducedpressure. The residual was extracted with CH₂Cl₂, washed with brine,dried with MgSO₄, filtered, and concentrated under reduced pressure. Theresidual was refined by column chromatography. The resultant product wassolidified using 2-propanol to obtain 5.0 g of Intermediate 11(3,6-di-tert-butyl-9-(4-(4,6-dichloro-1,3,5-triazin-2-yl)phenyl)-9H-carbazole)(Yield: 45%).

Synthesis of Intermediate 13

5.0 g (9.93 mmole) of Intermediate 11, 7.3 g (19.9 mmole) ofIntermediate 12, 215 mg (0.186 mmole) oftetrakis(triphenylphosphine)palladium(0) (Pd(PPh₃)₄), and 3.9 g (27.9mmole) of K₂CO₃ in 10 mL of a mixture including toluene and H₂O (avolumetric ratio of toluene to H₂O was 4:1) were heated under reducedpressure until the temperature reached a refluxing temperature. After areaction was completed, the mixture was cooled to room temperature,washed with brine, extracted with CH₂Cl₂, dried with anhydrous MgSO₄,filtered, and concentrated under reduced pressure. The residual wasrefined by using column chromatography to obtain 6.01 g of Intermediate(9,9′-((6-(4-(3,6-di-tert-butyl-9H-carbazol-9-yl)phenyl)-1,3,5-triazine-2,4-diyl)bis(4,1-phenylene))bis(9H-carbazole)(66%).

¹H-NMR (CDCl₃, 300 MHz): δ 8.99-7.28 (m, 34H), 1.54 (s, 18H)

¹³C-NMR (CDCl₃, 75 MHz): δ 171.3, 144.3, 143.0, 139.1, 138.7, 138.1,135.4, 129.7, 128.5, 127.2, 126.9, 123.7, 123.5, 116.3, 109.3, 34.8,32.0

Synthesis of Compound 3

392 mg (2.2 mmole) of NBS was dropped to 1.0 g (1.1 mmole) ofIntermediate 13 in 40 mL of a mixture including CHCl₃ and DMF (avolumetric ratio of CHCl₃ and DMF was 3:1) and a reaction was performedat room temperature. After the reaction was completed, the reactionmixture was washed with brine, extracted with CH₂Cl₂, dried withanhydrous MgSO₄, filtered, and concentrated under reduced pressure. Theresidual was refined by using column chromatography to obtain 1.1 g ofCompound 3(9,9′-((6-(4-(3,6-di-tert-butyl-9H-carbazol-9-yl)phenyl)-1,3,5-triazine-2,4-diyl)bis(4,1-phenylene))bis(3-bromo-9H-carbazole)(Yield: 89%).

Synthesis Example 4 Synthesis of Polymer 1

Polymer 1 having a repeating unit represented by the Polymer 1 formulain Reaction Scheme 4 below was synthesized according to Reaction Scheme4 below.

640 mg (2.325 mmol) of bis(1,5-cyclooctadiene) nickel (Ni(cod)₂), 363 mg(2.325 mmole) of 2,2′-bipyridyl, 1 g of Compound 3 (0.93 mmole), and 30mL of anhydrous THF were loaded into a reactor and the reactor waspurged with nitrogen. Polymerization was performed at a temperature of60° C. for 24 hours, bromobenzene as a terminal capping agent was addedto the reactor and then a reaction was performed for 24 hours. Thereaction product was purified with Florisil, precipitated with acetoneand methanol, and then dried under vacuum conditions for 24 hours toobtain Polymer 1.

GPC: Mw=3.6×10⁵, Mn=1.2×10⁵, PDI=3.0

Synthesis Example 5 Polymer 2

Polymer 2 including a repeating unit represented by the Polymer 2formula in Reaction Scheme 5 below was synthesized according to ReactionScheme 5 below.

500 mg (0.465 mmole) of Compound 3, 348 mg of (0.558 mmole) Compound 1,21 mg (0.093 mmole) of palladium acetate (Pd(OAc)₂), 81 mg (0.279 mmole)of tricyclohexylphosphine (P(Cy)₃) and 1.2 mL (2.33 mmole) of K₂CO₃ (2.0M in H₂O) were loaded into a flask together with Aliquat® 336 in 30 mLof toluene and gas-free water (through a syringe in a nitrogenatmosphere). The mixture was stirred, and heated at a temperature of100° C. for 24 hours. Then, 2-phenyl-1,3,2-dioxaborinane was added tothe obtained polymer and heated for 24 hours, and bromobenzene was addedthereto and heated for 24 hours, thereby capping the polymer. Theresultant polymer was refined by using Florisil and precipitated inacetone and methanol, and dried for 24 hours under vacuum conditions.

GPC: Mw=9.9×10³, Mn=5.0×10³, PDI=2.0

Synthesis Example 6 Synthesis of Polymer 3

Polymer 3 including a repeating unit represented by the Polymer 3formula in Reaction Scheme 6 below was synthesized according to ReactionScheme 6 below.

500 mg (0.465 mmole) of Compound 3, 554 mg (0.558 mmole) of Compound 2,21 mg (0.093 mmole) of Pd(OAc)₂, 81 mg (0.279 mmole) of P(Cy)₃, and 1.2mL (2.33 mmole) of K₂CO₃ (2.0 M in H₂O) were loaded into a flasktogether with Aliquat® 336 in 30 mL of toluene and gas-free water(through a syringe in a nitrogen atmosphere). The mixture was stirred,and heated at a temperature of 100° C. for 24 hours. Then,2-phenyl-1,3,2-dioxaborinane was added to the obtained polymer andheated for 24 hours, and bromobenzene was added thereto and heated for24 hours, thereby capping the polymer. The resultant polymer was refinedby using Florisil and precipitated in acetone and methanol, and driedfor 24 hours under vacuum conditions.

GPC: Mw=8.0×10³, Mn=4.2×10³, PDI=2.0

Evaluation Example 1 Evaluation of Luminescence Characteristics ofPolymers 1, 2, and 3 (in Solution State)

Luminescence characteristics of Polymers 1 to 3 were evaluated by usingan ultraviolet (UV) absorption spectrum and a photoluminescence (PL)spectrum. First, Polymer 1 was diluted to a concentration of 0.2 mM byusing toluene and a Shimadzu UV-350 spectrometer was used to measure aUV absorption spectrum. The same experiment was performed using Polymers2 and 3, and the results are shown in FIG. 2. Also, Polymer 1 wasdiluted to a concentration of 10 mM by using toluene and ISC PC1spectrofluorometer equipped with a Xenon lamp was used to measure a PLspectrum. The same experiment was performed using Polymers 2 and 3, andthe results are shown in FIG. 3.

Referring to FIGS. 2 and 3, it was confirmed that Polymers 2 and 3 insolution have excellent luminescence characteristics.

Example 1 An Organic Light-Emitting Device Including Polymer 1

A transparent electrode substrate manufactured by coating a glasssubstrate with indium-tin oxide (ITO) (having a thickness of 150 nm) wascleaned, and then the ITO layer was patterned to obtain a desired shapeby using a photosensitive resin and an etchant and then cleaned. A holetransport layer forming composition that included PEDOT (Batron P 4083manufactured by Bayer company), whose formula is shown below, was spincoated on the ITO layer, and then baked at a temperature of 200° C. forabout 0.5 hours, thereby forming a hole transport layer. An emittinglayer forming composition that included Polymer 1 and Ir(mppy)₃,Compound 15 below, (10 wt %) in chlorobenzene was spin coated on thehole transport layer, and then baked at a temperature of 120° C. for 30minutes, thereby forming an emitting layer including Polymer 1 andIr(mppy)₃. Each of the hole transport layer forming composition and theemitting layer forming composition was filtered with a 0.2 millimeter(mm) filter before spin coating. The thickness of the hole transportlayer and the emitting layer were adjusted to be 15 nm and 50 nmrespectively, by controlling a concentration of the correspondingcomposition and a spin coating rate. TPBi, whose formula is shown below,was vacuum deposited on the emitting layer while a vacuum pressure wasmaintained at 4×10⁻⁶ torr or less to form an electron transport layerhaving a thickness of 40 nm, and then, lithium fluoride (LiF) andaluminum (Al) were sequentially deposited on the electron transportlayer to form an electron injection layer (having a thickness of 1 nm)and a second electrode (having a thickness of 100 nm), therebycompleting manufacture of an organic light-emitting device. During thedeposition, a layer thickness and a layer growth rate were controlledusing a crystal sensor.

Example 2 An Organic Light-Emitting Device Including Polymer 2

An organic light-emitting device was manufactured in the same manner asin Example 1, except that Polymer 2 was used instead of Polymer 1 whenan emitting layer was formed.

Example 3 An Organic Light-Emitting Device Including Polymer 3

An organic light-emitting device was manufactured in the same manner asin Example 1, except that Polymer 3 was used instead of Polymer 1 whenan emitting layer was formed.

Comparative Example 1

An organic light-emitting device was manufactured in the same manner asin Example 1, except that a mixture including polyvinylcarbazole (“PVK”)(having a number average molecular weight (“Mn”) of 25,000 Daltons to50,000 Daltons and a PDI of 2) and4,4′-di(9H-carbazol-9-yl)-1,1′-biphenyl (“CBP”) (where a weight ratio ofPVK to CBP was 70:30) was used instead of Polymer 1 when an emittinglayer was formed.

The structure of each of the organic light-emitting devices manufacturedaccording to Examples 1 to 3 and Comparative Example 1 is shown in Table1.

TABLE 1 Electron Hole Electron injection transport transport layer/Anode layer Emitting layer layer cathode Exam- ITO PEDOT:P Polymer1:Ir(mppy)₃ TPBi LiF(1 nm)/ ple 1 (150 SS (10 wt. %)¹ (50 nm) (40 nm)Al(100 nm) nm) (15 nm) Exam- ITO PEDOT:P Polymer 2:Ir(mppy)₃ TPBi LiF(1nm)/ ple 2 (150 SS (10 wt. %)¹ (50 nm) (40 nm) Al(100 nm) nm (15 nm)Exam- ITO PEDOT:P Polymer 3:Ir(mppy)₃ TPBi LiF(1 nm)/ ple 3 (150 SS (10wt. %)¹ (50 nm) (40 nm) Al(100 nm) nm) (15 nm) Com- ITO PEDOT:PPVK:CBP¹:Ir(mppy)₃ TPBi LiF(1 nm)/ parative (150 SS (10 wt. %)² (50 nm)(40 nm) Al(100 nm) Exam- nm) (15 nm) ple 1 ¹A weight ratio of PVK to CBPis 70:30 ²Amount of Ir(mppy)₃ is evaluated based on 100 wt. % of thetotal weight of an emitting layer

Evaluation Example 2 Evaluation of Characteristics of OrganicLight-Emitting Device

Current density and brightness of each of the organic light-emittingdevices manufactured according to Examples 2 and 3 and ComparativeExample 1 were evaluated using a PR650 Spectroscan Source MeasurementUnit (Photo Research), and the results are shown in FIGS. 4 and 5.

Referring to FIGS. 4 and 5, it was confirmed that the organiclight-emitting devices including Polymers 2 and 3 manufactured accordingto Examples 2 and 3 respectively, had better current density andbrightness characteristics than the organic light-emitting devicemanufactured according to Comparative Example 1.

As described above, according to the one or more of the embodiments ofthis disclosure, the polymer including a repeating unit represented byFormula 1, has hole and electron transporting characteristics and hightriplet state energy. The organic light-emitting device including thepolymer has high efficiency, high current density, and high brightness.

It should be understood that the exemplary embodiments described hereinshould be considered in a descriptive sense only and not for purposes oflimitation. Descriptions of features or aspects within each embodimentshould typically be considered as available for other similar featuresor aspects in other embodiments.

1. A polymer comprising a repeating unit represented by Formula 1 below:

wherein, in Formula 1, in at least one pair of two R groups selectedfrom a pair R₁ and R₂, a pair R₃ and R₄, a pair R₅ and R₆, and a pair R₇and R₈, an atom in each R group thereof is connected to each other toform a single bond or connected to each other via a linking grouprepresented by —[C(Q₆)(Q₇)]_(p)-, or R₁ to R₈ are each independentlyhydrogen, deuterium, a halogen atom, a hydroxyl group, a cyano group, anitro group, a carboxyl group, a substituted or unsubstituted C₁-C₆₀alkyl group, a substituted or unsubstituted C₂-C₆₀ alkenyl group, asubstituted or unsubstituted C₂-C₆₀ alkynyl group, a substituted orunsubstituted C₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₆₀cycloalkyl group, a substituted or unsubstituted C₃-C₆₀ cycloalkenylgroup, a substituted or unsubstituted C₆-C₆₀ aryl group, a substitutedor unsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstitutedC₆-C₆₀ arylthio group, a substituted or unsubstituted C₁-C₆₀ heteroarylgroup, —N(Q₁)(Q₂) or —Si(Q₃)(Q₄)(Q₅); p is an integer of 1 or 2; Ar₁ toAr₃ are each independently a substituted or unsubstituted C₆-C₃₀ arylenegroup, or a substituted or unsubstituted C₁-C₃₀ heteroarylene group; a,b, and c are each independently an integer of 1 to 10; R₁₁ to R₃₉ areeach independently hydrogen, deuterium, a halogen atom, a hydroxylgroup, a cyano group, a nitro group, a carboxyl group, a substituted orunsubstituted C₁-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀ alkynyl group, asubstituted or unsubstituted C₁-C₆₀ alkoxy group, a substituted orunsubstituted C₃-C₆₀ cycloalkyl group, a substituted or unsubstitutedC₃-C₆₀ cycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₆-C₆₀ aryloxy group, asubstituted or unsubstituted C₆-C₆₀ arylthio group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, —N(Q₈)(Q₉), or—Si(Q₁₀)(Q₁₁)(Q₁₂); Q₁ to Q₁₂ are each independently hydrogen,deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitrogroup, a carboxyl group, a substituted or unsubstituted C₁-C₆₀ alkylgroup, a substituted or unsubstituted C₂-C₆₀ alkenyl group, asubstituted or unsubstituted C₂-C₆₀ alkynyl group, a substituted orunsubstituted C₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₆₀cycloalkyl group, a substituted or unsubstituted C₃-C₆₀ cycloalkenylgroup, a substituted or unsubstituted C₆-C₆₀ aryl group, a substitutedor unsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstitutedC₆-C₆₀ arylthio group, or a substituted or unsubstituted C₁-C₆₀heteroaryl group; and m is an integer of 0 to
 5. 2. The polymer of claim1, wherein in at least one pair selected from a pair R₁ and R₂, a pairR₃ and R₄, a pair R₅ and R₆, and a pair R₇ and R₈, an atom in each Rgroup are connected to each other to form a single bond or connected toeach other via a linking group represented by —[C(Q₆)(Q₇)]_(p)-, and Q₆and Q₇ are each independently hydrogen, deuterium, a halogen atom, ahydroxyl group, a cyano group, a nitro group, a carboxyl group, asubstituted or unsubstituted C₁-C₁₀ alkyl group, a substituted orunsubstituted C₂-C₁₀ alkenyl group, a substituted or unsubstitutedC₁-C₁₀ alkoxy group, a substituted or unsubstituted C₆-C₁₄ aryl group,or a substituted or unsubstituted C₁-C₁₄ heteroaryl group.
 3. Thepolymer of claim 1, wherein Ar₁ to Ar₃ are each independently asubstituted or unsubstituted phenylene group, a substituted orunsubstituted pentalenylene group, a substituted or unsubstitutedindenylene group, a substituted or unsubstituted naphthylene group, asubstituted or unsubstituted azulenylene group, a substituted orunsubstituted heptalenylene group, a substituted or unsubstitutedindacenylene group, a substituted or unsubstituted acenaphthylene group,a substituted or unsubstituted fluorenylene group, a substituted orunsubstituted phenanthrylene group, a substituted or unsubstitutedanthrylene group, a substituted or unsubstituted fluoranthenylene group,a substituted or unsubstituted triphenylenylene group, a substituted orunsubstituted pyrenylene group, a substituted or unsubstitutedchrysenylene group, a substituted or unsubstituted naphthacenylenegroup, a substituted or unsubstituted picenylene group, a substituted orunsubstituted perylenylene group, a substituted or unsubstitutedpentaphenylene group, a substituted or unsubstituted hexacenylene group,a substituted or unsubstituted pyrrolylene group, a substituted orunsubstituted pyrazolylene group, a substituted or unsubstitutedimidazolylene group, a substituted or unsubstituted imidazolinylenegroup, a substituted or unsubstituted imidazopyridinylene group, asubstituted or unsubstituted imidazopyrimidinylene group, a substitutedor unsubstituted pyridinylene group, a substituted or unsubstitutedpyrazinylene group, a substituted or unsubstituted pyrimidinylene group,a substituted or unsubstituted indolylene group, a substituted orunsubstituted purinylene group, a substituted or unsubstitutedquinolinylene group, a substituted or unsubstituted phthalazinylenegroup, a substituted or unsubstituted indolizinylene group, asubstituted or unsubstituted naphthyridinylene group, a substituted orunsubstituted quinazolinylene group, a substituted or unsubstitutedcinnolinylene group, a substituted or unsubstituted indazolylene group,a substituted or unsubstituted carbazolylene group, a substituted orunsubstituted phenazinylene group, a substituted or unsubstitutedphenanthridinylene group, a substituted or unsubstituted pyranylenegroup, a substituted or unsubstituted chromenylene group, a substitutedor unsubstituted benzofuranylene group, a substituted or unsubstitutedthiophenylene group, a substituted or unsubstituted benzothiophenylenegroup, a substituted or unsubstituted isothiazolylene group, asubstituted or unsubstituted benzoimidazolylene group, or a substitutedor unsubstituted isoxazolylene group.
 4. The polymer of claim 1, whereinAr₁ to Ar₃ are each independently a phenylene group, a (C₁-C₁₀alkyl)phenylene group, a di(C₁-C₁₀ alkyl)phenylene group, a (C₆-C₁₄aryl)phenylene group, a di(C₆-C₁₄ aryl)phenylene group, a fluorenylenegroup, a (C₁-C₁₀ alkyl)fluorenylene group, a di(C₁-C₁₀alkyl)fluorenylene group, a (C₆-C₁₄ aryl)fluorenylene group, a di(C₆-C₁₄aryl)fluorenylene group, a phenanthrylene group, a (C₁-C₁₀alkyl)phenanthrylene group, a di(C₁-C₁₀ alkyl)phenanthrylene group, a(C₆-C₁₄ aryl)phenanthrylene group, a di(C₆-C₁₄ aryl)phenanthrylenegroup, a pyridinylene group, a (C₁-C₁₀ alkyl)pyridinylene group, adi(C₁-C₁₀ alkyl)pyridinylene group, a (C₆-C₁₄ aryl)pyridinylene group,or a di(C₆-C₁₄ aryl)pyridinylene group.
 5. The polymer of claim 1,wherein a, b, and c are each independently 1, 2, 3, or
 4. 6. The polymerof claim 1, wherein R₁₁ to R₃₉ are each independently hydrogen,deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitrogroup, a carboxyl group, a substituted or unsubstituted C₁-C₁₀ alkylgroup, a substituted or unsubstituted C₂-C₁₀ alkenyl group, asubstituted or unsubstituted C₁-C₁₀ alkoxy group, a substituted orunsubstituted C₆-C₁₄ aryl group, or a substituted or unsubstitutedC₁-C₁₄ heteroaryl group.
 7. The polymer of claim 1, wherein R₁₁ to R₁₉,R²¹ to R₂₃, and R₂₅ to R₃₈ are all hydrogen, and R₂₀, R₂₄ and R₃₉ areeach independently hydrogen, deuterium, a halogen atom, a hydroxylgroup, a cyano group, a nitro group, a carboxyl group, a substituted orunsubstituted C₁-C₁₀ alkyl group, a substituted or unsubstituted C₂-C₁₀alkenyl group, a substituted or unsubstituted C₁-C₁₀ alkoxy group, asubstituted or unsubstituted C₆-C₁₄ aryl group, or a substituted orunsubstituted C₁-C₁₄ heteroaryl group.
 8. The polymer of claim 1,wherein m is 0, 1, or
 2. 9. The polymer of claim 1, wherein therepeating unit is represented by Formula 1A, 1B, or 1C below:

wherein, in Formulae 1A, 1B, and 1C, R₁₁ to R₃₉ and Q₆ and Q₇ are eachindependently hydrogen, deuterium, a halogen atom, a hydroxyl group, acyano group, a nitro group, a carboxyl group, a substituted orunsubstituted C₁-C₁₀ alkyl group, a substituted or unsubstituted C₂-C₁₀alkenyl group, a substituted or unsubstituted C₁-C₁₀ alkoxy group, asubstituted or unsubstituted C₆-C₁₄ aryl group, or a substituted orunsubstituted C₁-C₁₄ heteroaryl group; Ar₁ to Ar₃ are each independentlya substituted or unsubstituted phenylene group, a substituted orunsubstituted fluorenylene group, a substituted or unsubstitutedphenanthrylene group, or a substituted or unsubstituted pyridinylenegroup, or a substituted or unsubstituted phenylpyridinylene group; a, b,and c are each independently an integer of 1 to 10; and m is 0, 1, or 2.10. The polymer of claim 9, wherein R₁₁ to R₁₉, R₂₁ to R₂₃, and R₂₅ toR₃₈ are all hydrogen, and R₂₀, R₂₄, and R₃₉ are each independentlyhydrogen, deuterium, a halogen atom, a hydroxyl group, a cyano group, anitro group, a carboxyl group, a substituted or unsubstituted C₁-C₁₀alkyl group, a substituted or unsubstituted C₂-C₁₀ alkenyl group, asubstituted or unsubstituted C₁-C₁₀ alkoxy group, a substituted orunsubstituted C₆-C₁₄ aryl group, or a substituted or unsubstitutedC₁-C₁₄ heteroaryl group.
 11. The polymer of claim 9, wherein Ar₁ to Ar₃are each independently a phenylene group, a fluorenylene group, aphenanthrylene group, a pyridinylene group, or a phenyl-pyridinylenegroup; and a, b, and c are each independently 1, 2, 3, or
 4. 12. Thepolymer of claim 1, wherein the repeating unit is represented by Formula1A-1 below:

wherein, in Formula 1A-1, R₂₀, R₂₄ and R₃₉ are each independentlyhydrogen, deuterium, a halogen atom, a hydroxyl group, a cyano group, anitro group, a carboxyl group, a C₁-C₁₀ alkyl group, or a C₁-C₁₀ alkoxygroup; Ar₁ to Ar₃ are each independently a substituted or unsubstitutedphenylene group, a substituted or unsubstituted fluorenylene group, asubstituted or unsubstituted phenanthrylene group, a substituted orunsubstituted pyridinylene group, or a substituted or unsubstitutedphenylpyridinylene group; a, b, and c are each independently 1, 2, 3 or4; and m is 0, 1, or
 2. 13. The polymer of claim 1, wherein R₁ to R₈ areidentical to each other.
 14. The polymer of claim 1, wherein R₁ to R₈are each independently hydrogen, deuterium, a halogen atom, a hydroxylgroup, a cyano group, a nitro group, a carboxyl group, a C₁-C₁₀ alkylgroup, or a C₁-C₁₀ alkoxy group.
 15. The polymer of claim 1, wherein aweight average molecular weight of the polymer is about 2,000 Daltons toabout 1,000,000 Daltons.
 16. The polymer of claim 1, wherein the polymeris a bipolar polymer that functions as a phosphorescent host.
 17. Anorganic light-emitting device comprising a substrate; a first electrode;a second electrode; and a first layer disposed between the firstelectrode and the second electrode, wherein the first layer comprisesthe polymer of claim
 1. 18. The organic light-emitting device of claim17, wherein the first layer is an emitting layer and further comprises aphosphorescent dopant.
 19. The organic light-emitting device of claim18, wherein the phosphorescent dopant is an organometallic complexcomprising iridium, platinum, osmium, rhenium, titanium, zirconium,hafnium, or a combination thereof.
 20. The organic light-emitting deviceof claim 18, wherein an amount of the phosphorescent dopant in the firstlayer is about 1 wt. % to about 10 wt. % based on the total weight ofthe first layer.